Chicago lines its lakefront with miles of urban beaches

DAY 2 | Those green roofs you saw are only a fraction of Chicago’s copious green space. Today you explore deeper, starting with brunch at North Pond (1), a James Beard–winning eatery inside Lincoln Park (2). This place has been using local, organic food on its seasonally inspired menu since before such conceits were hip. Watch a parade of big, shaggy dogs walk around the pond as you dig into your crispy trout. After the meal, you stroll through the park, taking time to check out the Green City Market (3), a massive farmers market with vendors selling a host of locally grown or produced goods, from carrots to cheese to wheatgrass juice. Sipping a healthy brew, you wander past Lincoln Park Zoo, home to 1,200 species and an antique carousel. Gradually you’re drawn to the grand old buildings of Lincoln Park. You drift into independent book and music shops (remember those?) and begin to see why this neighborhood is so beloved by locals. The sun filters through the trees and onto your face, and you to realize it’s well past noon and you’re hungry again.

Part of the reason you’re in Chicago is the storied deep-dish pizza. Uno’s and Gino’s East are the most famous, but locals tell you that Lou Malnati’s (4), with its light, flaky “Buttercrust” topped with thick sauce and fresh mozzarella, is the best. So you hop in a cab, brave the gregarious crowds and fill up on rich pie topped with perfectly spiced sausage.

Now you’re ready to explore another trendy neighborhood, Wicker Park (5). Once a working-class burg, it’s now a haven for creative twenty some things who—much as you’re about to do—fritter away afternoons in vintage shops and boutiques ranging from high-end (Alexis Bittar jewelry) to affordable (Akira clothing). You peek into the Flat Iron Arts building at the intersection of Damen and North avenues, filled with artist studios open to the public, then stop by the actual park to cool off by the granite and cast-iron fountain, which was erected in the 1890s and restored in 2002.

You head off to dinner at Girl & the Goat (6). Helmed by Top Chef Winner Stephanie Izard and nominated for a James Beard award, Girl & the Goat is one of the hottest restaurants in town. The menu is divided into vegetable, fish and meat sections, and the dishes are meant to be shared family-style. You munch on the simple roast cauliflower with pickled peppers, marveling that something so straightforward can be so delicious.

Not ready to end the night just yet, you make a stop at Leopold (7), a Belgian-style bar, where you relax in the lounge sipping the perfectly refreshing Lost in Flanders cocktail of Leopold Brothers (no relation) boutique gin, elderflower liqueur, house made lemon bitters and basil syrup. Watching people of all ages and walks of life mingle, you feel perfectly at home, but have to call it a night before your next action-packed day.